Run these commands to add both certs to Java cacerts.

keytool -import -trustcacerts -cacerts

-storepass changeit -noprompt -alias lktPrivateCertRoot -file D:\LookoutPrivateCARoot.crt

keytool -import -trustcacerts -cacerts

-storepass changeit -noprompt -alias lktFwdProxy -file D:\lookoutforwardproxy.crt

Import the Root cert to the Git CLI by adding the LookoutPrivateCARoot.crt content to the end of the ca-bundle.crt file in the Git installation:

<GIT_INSTALL_LOCATION > \ming

w64\etc\ssl\certs\ca-bundle.crt

sudo keytool -import -keystore cacerts -trustcacerts -alias your-alias-here -file path/to/certificate.cer
Example:
sudo keytool -import -keystore cacerts -trustcacerts -alias lookoutcert -file
/Users/tonykelly/downloads/look outokta.net.pem
Validate CLI / GitHub config
git config --global http.sslCaInfo

Import the Root cert to Aws CLI.

Add the LookoutPrivateCARoot.crt file content to the end of the cacert.pem file in the AWS CLI installation location.

C:\Program Files\Amazon\AWSCLIV2\awscli\b otocore\cacert.pem.

sudo keytool -import -keystore cacerts

-trustcacerts -alias your-alias-here -file path/to/certificate.cer

Example:

sudo keytool -import -keystore cacerts -trustcacerts -alias lookoutcert -file
/Users/tonykelly/downloads/look outokta.net.cer

Find the location of the truststore.

$ python -c "import certifi;print(certifi.where ());"

C:\Python311\Lib\site-packages\certifi

\cacert.pem

Add the content of LookoutPrivateCARoot.crt at the end of the cacert.pem file.

If you are using PIP, run this command:

python -m pip config set global.cert path/to/cacert.pem

sudo keytool -import -keystore cacerts -trustcacerts -alias
your-alias-here -file path/to/certificate.cer

Example:

sudo keytool -import -keystore cacerts -trustcacerts -alias lookoutcert -file
/Users/tonykelly/downloads/look outokta.net.cer

Export certs as described in Step 1:

to ~/LookoutPrivateCARoot.crt and

~/lookoutforwardproxy.crt

Combine the certs:

cat LookoutPrivateCARoot.crt lookoutforwardproxy.crt > lookoutcombined.pem

Configure the GCP custom ca certs: gcloud config set core/custom_ca_certs_file

~/lookoutcombined.pem